JP2010535816A - ヘテロアリールアミド類似体 - Google Patents

Info

Publication number

JP2010535816A

JP2010535816A JP2010520343A JP2010520343A JP2010535816A JP 2010535816 A JP2010535816 A JP 2010535816A JP 2010520343 A JP2010520343 A JP 2010520343A JP 2010520343 A JP2010520343 A JP 2010520343A JP 2010535816 A JP2010535816 A JP 2010535816A

Authority

JP

Japan

Prior art keywords

alkyl

indole

pyrimidin

carboxamide

methyl

Prior art date

2007-08-10

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

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• Global Dossier
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• -1 Heteroaryl amide Chemical class 0.000 title claims abstract description 114
• 150000001875 compounds Chemical class 0.000 claims abstract description 262
• 102000005962 receptors Human genes 0.000 claims abstract description 120
• 108020003175 receptors Proteins 0.000 claims abstract description 120
• 208000002193 Pain Diseases 0.000 claims abstract description 86
• 230000036407 pain Effects 0.000 claims abstract description 77
• 238000000034 method Methods 0.000 claims abstract description 60
• 208000024891 symptom Diseases 0.000 claims abstract description 37
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 29
• 239000000556 agonist Substances 0.000 claims abstract description 27
• 206010061218 Inflammation Diseases 0.000 claims abstract description 19
• 230000004054 inflammatory process Effects 0.000 claims abstract description 19
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 7
• 208000030533 eye disease Diseases 0.000 claims abstract description 6
• 208000026278 immune system disease Diseases 0.000 claims abstract description 5
• 239000000203 mixture Substances 0.000 claims description 90
• 150000003839 salts Chemical class 0.000 claims description 79
• 125000000217 alkyl group Chemical group 0.000 claims description 78
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 71
• 230000000694 effects Effects 0.000 claims description 67
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
• 229910052736 halogen Inorganic materials 0.000 claims description 46
• 150000002367 halogens Chemical class 0.000 claims description 45
• 238000003556 assay Methods 0.000 claims description 44
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 43
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
• 125000001424 substituent group Chemical group 0.000 claims description 42
• 210000004027 cell Anatomy 0.000 claims description 38
• 125000001072 heteroaryl group Chemical group 0.000 claims description 34
• 238000011282 treatment Methods 0.000 claims description 33
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 32
• 125000004432 carbon atom Chemical group C* 0.000 claims description 32
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 31
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 30
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
• 239000001257 hydrogen Substances 0.000 claims description 28
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• 125000003118 aryl group Chemical group 0.000 claims description 26
• 125000002947 alkylene group Chemical group 0.000 claims description 25
• 208000004296 neuralgia Diseases 0.000 claims description 24
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 23
• 229910052799 carbon Inorganic materials 0.000 claims description 23
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000002837 carbocyclic group Chemical group 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 18
• 125000004043 oxo group Chemical group O=* 0.000 claims description 17
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 15
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
• 206010016654 Fibrosis Diseases 0.000 claims description 14
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
• 238000000338 in vitro Methods 0.000 claims description 14
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 14
• 125000004429 atom Chemical group 0.000 claims description 13
• 208000006673 asthma Diseases 0.000 claims description 12
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
• 208000021722 neuropathic pain Diseases 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
• 230000004761 fibrosis Effects 0.000 claims description 10
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 208000011580 syndromic disease Diseases 0.000 claims description 10
• 239000003826 tablet Substances 0.000 claims description 10
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 9
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
• 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 9
• 206010029240 Neuritis Diseases 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 201000001119 neuropathy Diseases 0.000 claims description 9
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 9
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 8
• 210000005036 nerve Anatomy 0.000 claims description 8
• 230000007823 neuropathy Effects 0.000 claims description 8
• 208000024827 Alzheimer disease Diseases 0.000 claims description 7
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 7
• 150000005215 alkyl ethers Chemical class 0.000 claims description 7
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 7
• 201000010099 disease Diseases 0.000 claims description 7
• 201000008482 osteoarthritis Diseases 0.000 claims description 7
• 239000000126 substance Substances 0.000 claims description 7
• 208000023275 Autoimmune disease Diseases 0.000 claims description 6
• 230000001154 acute effect Effects 0.000 claims description 6
• 125000004423 acyloxy group Chemical group 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 6
• 210000003169 central nervous system Anatomy 0.000 claims description 6
• 239000006071 cream Substances 0.000 claims description 6
• 239000000499 gel Substances 0.000 claims description 6
• 238000000099 in vitro assay Methods 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 210000003994 retinal ganglion cell Anatomy 0.000 claims description 6
• 238000006467 substitution reaction Methods 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 208000008035 Back Pain Diseases 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 5
• 206010003246 arthritis Diseases 0.000 claims description 5
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
• 230000034994 death Effects 0.000 claims description 5
• 238000002347 injection Methods 0.000 claims description 5
• 239000007924 injection Substances 0.000 claims description 5
• 208000014674 injury Diseases 0.000 claims description 5
• 206010025135 lupus erythematosus Diseases 0.000 claims description 5
• 230000009529 traumatic brain injury Effects 0.000 claims description 5
• 208000010412 Glaucoma Diseases 0.000 claims description 4
• 201000005569 Gout Diseases 0.000 claims description 4
• 206010019233 Headaches Diseases 0.000 claims description 4
• 206010039710 Scleroderma Diseases 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 230000001684 chronic effect Effects 0.000 claims description 4
• 230000007882 cirrhosis Effects 0.000 claims description 4
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
• 231100000869 headache Toxicity 0.000 claims description 4
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
• 230000036571 hydration Effects 0.000 claims description 4
• 238000006703 hydration reaction Methods 0.000 claims description 4
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 229910052721 tungsten Inorganic materials 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• FPHOPYWEFQYZLM-UHFFFAOYSA-N 1-[(1-methylimidazol-2-yl)methyl]-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-2-carboxamide Chemical compound CN1C=CN=C1CN1C2=CC=CC=C2C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 FPHOPYWEFQYZLM-UHFFFAOYSA-N 0.000 claims description 3
• ATWCIOGPHPGOGT-UHFFFAOYSA-N 2-(1-adamantyl)-n-(4-chloro-1-pyrimidin-2-ylindol-3-yl)acetamide Chemical compound C1=C(NC(=O)CC23CC4CC(CC(C4)C2)C3)C=2C(Cl)=CC=CC=2N1C1=NC=CC=N1 ATWCIOGPHPGOGT-UHFFFAOYSA-N 0.000 claims description 3
• VEEYSQAYZKOZIT-UHFFFAOYSA-N 4-chloro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 VEEYSQAYZKOZIT-UHFFFAOYSA-N 0.000 claims description 3
• ANAIABPQJGVDQA-UHFFFAOYSA-N 4-chloro-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=2C(Cl)=CC=NC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 ANAIABPQJGVDQA-UHFFFAOYSA-N 0.000 claims description 3
• 208000004998 Abdominal Pain Diseases 0.000 claims description 3
• 206010023230 Joint stiffness Diseases 0.000 claims description 3
• 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 3
• 230000002159 abnormal effect Effects 0.000 claims description 3
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
• 239000000443 aerosol Substances 0.000 claims description 3
• 230000008484 agonism Effects 0.000 claims description 3
• 239000002775 capsule Substances 0.000 claims description 3
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
• 230000008859 change Effects 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000003106 haloaryl group Chemical group 0.000 claims description 3
• JZYSYXDHRXPHKQ-UHFFFAOYSA-N n-(1-adamantylmethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C(C1=CC=CC=C11)=CN1C1=NC=CC=N1 JZYSYXDHRXPHKQ-UHFFFAOYSA-N 0.000 claims description 3
• YJCCGSIXSDHVLI-UHFFFAOYSA-N n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-yl-4-(trifluoromethyl)indole-3-carboxamide Chemical compound C1=2C(C(F)(F)F)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 YJCCGSIXSDHVLI-UHFFFAOYSA-N 0.000 claims description 3
• ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 238000001356 surgical procedure Methods 0.000 claims description 3
• 239000006188 syrup Substances 0.000 claims description 3
• 235000020357 syrup Nutrition 0.000 claims description 3
• 150000003536 tetrazoles Chemical class 0.000 claims description 3
• 230000008733 trauma Effects 0.000 claims description 3
• 206010002383 Angina Pectoris Diseases 0.000 claims description 2
• 206010058019 Cancer Pain Diseases 0.000 claims description 2
• 208000001387 Causalgia Diseases 0.000 claims description 2
• 208000002881 Colic Diseases 0.000 claims description 2
• 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims description 2
• 206010014020 Ear pain Diseases 0.000 claims description 2
• 206010015958 Eye pain Diseases 0.000 claims description 2
• 206010016059 Facial pain Diseases 0.000 claims description 2
• 208000033830 Hot Flashes Diseases 0.000 claims description 2
• 206010060800 Hot flush Diseases 0.000 claims description 2
• 208000000112 Myalgia Diseases 0.000 claims description 2
• 206010049002 Scar pain Diseases 0.000 claims description 2
• 206010072005 Spinal pain Diseases 0.000 claims description 2
• 206010042496 Sunburn Diseases 0.000 claims description 2
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
• 230000008485 antagonism Effects 0.000 claims description 2
• 208000003295 carpal tunnel syndrome Diseases 0.000 claims description 2
• 208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims description 2
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
• 201000006549 dyspepsia Diseases 0.000 claims description 2
• 239000012530 fluid Substances 0.000 claims description 2
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 2
• 125000005059 halophenyl group Chemical group 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
• 208000013465 muscle pain Diseases 0.000 claims description 2
• 230000008764 nerve damage Effects 0.000 claims description 2
• 201000009985 neuronitis Diseases 0.000 claims description 2
• 150000002825 nitriles Chemical group 0.000 claims description 2
• 230000000414 obstructive effect Effects 0.000 claims description 2
• 239000006187 pill Substances 0.000 claims description 2
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
• 230000008653 root damage Effects 0.000 claims description 2
• 230000001953 sensory effect Effects 0.000 claims description 2
• 239000002435 venom Substances 0.000 claims description 2
• 210000001048 venom Anatomy 0.000 claims description 2
• 231100000611 venom Toxicity 0.000 claims description 2
• 208000009935 visceral pain Diseases 0.000 claims description 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
• TZKDHXJYDQGLFK-UHFFFAOYSA-N 4-chloro-n-[2-(3,4-difluorophenyl)-2-piperidin-1-ylethyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=C(F)C(F)=CC=C1C(N1CCCCC1)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 TZKDHXJYDQGLFK-UHFFFAOYSA-N 0.000 claims 2
• 230000002401 inhibitory effect Effects 0.000 claims 2
• LKMRWAUYFFIPLS-UHFFFAOYSA-N 1-(3-cyanopyridin-2-yl)-4-methyl-n-(2-morpholin-4-yl-2-phenylethyl)indole-3-carboxamide Chemical compound C1=2C(C)=CC=CC=2N(C=2C(=CC=CN=2)C#N)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 LKMRWAUYFFIPLS-UHFFFAOYSA-N 0.000 claims 1
• JCSUYDVTWQJBCI-UHFFFAOYSA-N 1-(3-ethylpyrazin-2-yl)-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-3-carboxamide Chemical compound CCC1=NC=CN=C1N1C2=CC=CC=C2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=C1 JCSUYDVTWQJBCI-UHFFFAOYSA-N 0.000 claims 1
• DVQJAIGHURJMKU-UHFFFAOYSA-N 1-(5-fluoropyrimidin-2-yl)-n-[(1-pyridin-3-ylcyclohexyl)methyl]indole-3-carboxamide Chemical compound N1=CC(F)=CN=C1N1C2=CC=CC=C2C(C(=O)NCC2(CCCCC2)C=2C=NC=CC=2)=C1 DVQJAIGHURJMKU-UHFFFAOYSA-N 0.000 claims 1
• FLPKUPFRCHXLDY-UHFFFAOYSA-N 1-pyrimidin-2-yl-n-[[1-[4-(trifluoromethyl)phenyl]cyclohexyl]methyl]indole-3-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1(CNC(=O)C=2C3=CC=CC=C3N(C=3N=CC=CN=3)C=2)CCCCC1 FLPKUPFRCHXLDY-UHFFFAOYSA-N 0.000 claims 1
• GGNNKOPRPONVQA-UHFFFAOYSA-N 1-pyrimidin-2-ylindole-3,4-dicarboxylic acid Chemical compound C12=CC=CC(C(O)=O)=C2C(C(=O)O)=CN1C1=NC=CC=N1 GGNNKOPRPONVQA-UHFFFAOYSA-N 0.000 claims 1
• STSVLKXCUGQLSX-UHFFFAOYSA-N 2-[3-(1-adamantylmethylcarbamoyl)indol-1-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N1C2=CC=CC=C2C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 STSVLKXCUGQLSX-UHFFFAOYSA-N 0.000 claims 1
• RVHSUIQQODJJDG-UHFFFAOYSA-N 2-[3-(1-adamantylmethylcarbamoyl)indol-1-yl]pentanoic acid Chemical compound C12=CC=CC=C2N(C(C(O)=O)CCC)C=C1C(=O)NCC1(C2)CC(C3)CC2CC3C1 RVHSUIQQODJJDG-UHFFFAOYSA-N 0.000 claims 1
• LCLKNJIWBCOANV-UHFFFAOYSA-N 3-chloro-1-[(1-methylimidazol-2-yl)methyl]-n-(4-methyl-2-pyridin-3-ylpentyl)indole-2-carboxamide Chemical compound C=1C=CN=CC=1C(CC(C)C)CNC(=O)C1=C(Cl)C2=CC=CC=C2N1CC1=NC=CN1C LCLKNJIWBCOANV-UHFFFAOYSA-N 0.000 claims 1
• YZFMHZXAUUEHDM-UHFFFAOYSA-N 3-chloro-n-[2-(4-chlorophenyl)-2-piperidin-1-ylethyl]-1-[(1-methylimidazol-2-yl)methyl]indole-2-carboxamide Chemical compound CN1C=CN=C1CN1C2=CC=CC=C2C(Cl)=C1C(=O)NCC(C=1C=CC(Cl)=CC=1)N1CCCCC1 YZFMHZXAUUEHDM-UHFFFAOYSA-N 0.000 claims 1
• QYDVTNYUERGOIZ-UHFFFAOYSA-N 3-chloro-n-[[4-(4-chlorophenyl)oxan-4-yl]methyl]-1-[(1-methylimidazol-2-yl)methyl]indole-2-carboxamide Chemical compound CN1C=CN=C1CN1C2=CC=CC=C2C(Cl)=C1C(=O)NCC1(C=2C=CC(Cl)=CC=2)CCOCC1 QYDVTNYUERGOIZ-UHFFFAOYSA-N 0.000 claims 1
• GHPANTLFSOVSKV-UHFFFAOYSA-N 4-bromo-n-[(1-pyridin-3-ylcyclohexyl)methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Br)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 GHPANTLFSOVSKV-UHFFFAOYSA-N 0.000 claims 1
• SZMUXKSFYOVBLZ-UHFFFAOYSA-N 4-chloro-1-[2-(dimethylamino)ethyl]-n-(4-methyl-2-pyridin-3-ylpentyl)indole-3-carboxamide Chemical compound C=1N(CCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=CN=C1 SZMUXKSFYOVBLZ-UHFFFAOYSA-N 0.000 claims 1
• KCGVNAOUYOFNIB-UHFFFAOYSA-N 4-chloro-1-[3-(dimethylamino)propyl]-n-(4-methyl-2-pyridin-3-ylpentyl)indole-3-carboxamide Chemical compound C=1N(CCCN(C)C)C2=CC=CC(Cl)=C2C=1C(=O)NCC(CC(C)C)C1=CC=CN=C1 KCGVNAOUYOFNIB-UHFFFAOYSA-N 0.000 claims 1
• FTKQORPRCLRPNX-UHFFFAOYSA-N 4-chloro-1-pyrimidin-2-yl-n-(3,3,5-trimethylcyclohexyl)indole-3-carboxamide Chemical compound C1C(C)(C)CC(C)CC1NC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 FTKQORPRCLRPNX-UHFFFAOYSA-N 0.000 claims 1
• GBQVSGPQEXAYLT-VMBOVVBDSA-N 4-chloro-N-[[(1R)-6,6-dimethyl-2-bicyclo[3.1.1]heptanyl]methyl]-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C([C@]1(C2(C)C)[H])C2CCC1CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 GBQVSGPQEXAYLT-VMBOVVBDSA-N 0.000 claims 1
• LRSPAPPWXYSXKT-UHFFFAOYSA-N 4-chloro-n-(2,3-diphenylpropyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)CC1=CC=CC=C1 LRSPAPPWXYSXKT-UHFFFAOYSA-N 0.000 claims 1
• WSPSZBVPJYACII-UHFFFAOYSA-N 4-chloro-n-(2-cyclohexyl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)C1CCCCC1 WSPSZBVPJYACII-UHFFFAOYSA-N 0.000 claims 1
• YTJSTQCNEZOXLZ-UHFFFAOYSA-N 4-chloro-n-(2-morpholin-4-yl-2-phenylethyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 YTJSTQCNEZOXLZ-UHFFFAOYSA-N 0.000 claims 1
• WXIVLUUFVMVXNN-UHFFFAOYSA-N 4-chloro-n-(2-morpholin-4-yl-2-phenylethyl)-1-pyrimidin-2-ylpyrrolo[2,3-b]pyridine-3-carboxamide Chemical compound C1=2C(Cl)=CC=NC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)N1CCOCC1 WXIVLUUFVMVXNN-UHFFFAOYSA-N 0.000 claims 1
• QKSVJBHORLUNPE-UHFFFAOYSA-N 4-chloro-n-(2-phenylpentyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C=1C=CC=CC=1C(CCC)CNC(=O)C(C1=C(Cl)C=CC=C11)=CN1C1=NC=CC=N1 QKSVJBHORLUNPE-UHFFFAOYSA-N 0.000 claims 1
• RGVNVQZTKWHPNU-UHFFFAOYSA-N 4-chloro-n-(3-cyclopentyl-2-phenylpropyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C1=2C(Cl)=CC=CC=2N(C=2N=CC=CN=2)C=C1C(=O)NCC(C=1C=CC=CC=1)CC1CCCC1 RGVNVQZTKWHPNU-UHFFFAOYSA-N 0.000 claims 1
• NQIVGAXWGWVAGP-UHFFFAOYSA-N 4-chloro-n-(3-methylbutyl)-1-pyrimidin-2-ylindole-3-carboxamide Chemical compound C12=CC=CC(Cl)=C2C(C(=O)NCCC(C)C)=CN1C1=NC=CC=N1 NQIVGAXWGWVAGP-UHFFFAOYSA-N 0.000 claims 1
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